From Misfit to This Fits: My Entrepreneurial Journey

Written for EO by Kate Holden, an entrepreneur, philanthropist and business leader behind De Luca Fine Wines, a fast-growing retail and e-commerce wine business. Kate is president of the EO Winnipeg chapter and serves on the EO Canada Board as Canada’s MPD (Member Products Director).

As a kid, I grew up feeling different than everybody else.

Some of my most vivid childhood memories consist of a constant stream of questions, asking me “why” I was the way I was. My mother would get calls from the principal because I was secretly wearing makeup in grade 4. “Why do you have to be … different?” she would ask me.

Later in my youth and into adulthood, questions around why I was the way I was continued to follow me:

  • Why do you wear so much makeup?
  • Why are you always in heels?
  • Why is your hair always done?

I was the friend, the co-worker, the acquaintance who put a puzzled, vexed look on faces everywhere I went. I noticed my expectations were higher than others’. My career ambitions were different, too: I had dreams of owning my own business and building something of my own. More questions came.

I spent years feeling misplaced, uncomfortable with many people, and not fitting in many environments. I started to question myself, wondering why my views, feelings and standards were so different.

Then, I became an entrepreneur.

In my company’s early years, I was immersed in the “bubble” of my business. As time passed and the business grew, I began to meet other entrepreneurs, and that’s how I discovered EO. For the first time, suddenly, I found myself fitting in. There were others just like me!

There were three clear signs which helped me realize that I had finally found my people.

1. Intentionality

The tendency of entrepreneurs to want to be “in control” is not new. But joining EO showed me that other entrepreneurs craved more than just control; they were obsessed with creating “a life by design.” It wasn’t about being a control-freak over one’s company (although that often happens, too); it was about being firmly in the driver’s seat with every aspect of one’s life. It was about being intentional.

I realized that for so many entrepreneurs, “design” was a mindset: our lives and businesses could be designed with the right series of decisions, habits, systems, processes and frameworks. I met entrepreneurs who were running automated dashboards and Excel spreadsheets on everything from their company revenue to their weight loss goals to their family relationships. It wasn’t about controlling things for the sake of control; it was about applying structure to engineer the best version of our lives and work. I related.

2. Extra-ness

In EO, I met entrepreneurs who were “one level extra”―just like I was. Excessive, over-the-top, taking risks and operating on speeds and levels that you don’t often see in the regular world. Suddenly, it wasn’t just okay to be “extra”; it was … encouraged. It seemed to be the way all entrepreneurs operated.

Eventually, I learned the real and concerning statistics around entrepreneurship and mental health issues, depression and substance abuse. Entrepreneurship groups would function as both an accountability structure and a support community to keep each other in-check, as if so many entrepreneurs were on the edge of drinking too much, becoming obsessive over the wrong things, or crashing their businesses into oblivion. Some are too smart, passionate and excessive for their own good. A little like I had always been.

I learned that the right amount of “being extra” could directly contribute to massive entrepreneurial success; and the wrong amount could be the downfall into spiraling struggle. Everywhere around me, entrepreneurs were walking a tightrope, trying not to slip and fall into an abyss. I saw myself in that tightrope-walk.

3. Growth and change

The entrepreneurs around me exhibit a true passion and thirst for learning. Some are reading 50 to 100 books each year. Whether attending presentations, signing up for new courses or coaching programs, adopting new skills and refining old ones―the learning and self-development is nonstop. New systems, new processes, new methodologies, new everything. In a matter of weeks, I hear about entire business models being changed, websites being launched, and products going from concept to in-market.

In EO, change is the only constant. An obsession with learning, pushing the self, pushing others and growth is refreshing. I was never satisfied with having a “good company” or living a “nice life.” I always wanted the best: To build the best and to be the best. I always wanted to be a better business owner, team leader, wife, mother and friend than I was yesterday. My fellow EOers are the same.

EO: My home sweet home

Ultimately, I found a home in entrepreneurship, among other entrepreneurs.

But outside of EO, another “why” question surfaced: “Why are you like this now? Why have you changed?”

Originally, I took it as an insult (and maybe it was meant as such).

But after spending years around some of the most inspiring, excessive, passionate, tightrope-walking entrepreneurs in the world, I could only hope I have changed from the person I was before.

If you’re an entrepreneur, the next time someone asks you, “Wow, why does it seem like you’ve changed?”―be sure to take it as the ultimate compliment. It means you’re spending enough time with the right people, going down the harder roads, learning nonstop, being passionately excessive, and living a life by design.

It’s the first “why” question I’ve ever loved hearing. Go ahead―ask me why I’ve changed. I might ask you why you haven’t.

For more insights and inspiration from today’s leading entrepreneurs, check out EO on Inc. and more articles from the EO blog

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